CH234926A - Process for the preparation of a reactive ester of an oxyalkylamidine. - Google Patents

Process for the preparation of a reactive ester of an oxyalkylamidine.

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Publication number
CH234926A
CH234926A CH234926DA CH234926A CH 234926 A CH234926 A CH 234926A CH 234926D A CH234926D A CH 234926DA CH 234926 A CH234926 A CH 234926A
Authority
CH
Switzerland
Prior art keywords
sep
received
same
oxyalkylamidine
preparation
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH234926A publication Critical patent/CH234926A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Darstellung eines reaktionsfähigen Esters eines     Oayalkylamidins.       Es     wurde    gefunden, dass man zu einem  neuen reaktionsfähigen Ester eines     Oxyalkyl-          amidins    gelangen kann, wenn man einen       Bromacetimidoäther    mit     Athylendiamin    um  setzt. Zweckmässig     arbeitet    man in Gegen  wart eines     Lösungsmittels.     



  Das so gewonnene     2-Brommethyl-imid-          azolin    der Formel  
EMI0001.0011     
    bildet ein farbloses     Hydrobromid    vom F. 206  bis 209 . In Wasser ist es leicht löslich. Es  soll als Zwischenprodukt Verwendung finden.  <I>Beispiel:</I>  In eine Lösung von 30 Teilen     Bromaceto-          nitril    und 11,5 Teilen absolutem Alkohol in  300 Teilen absolutem Äther leitet man 20, g       Bromwa.sserstoffsäure    ein und     lässt    das Ge  misch 7 Stunden bei -1'0  stehen.

   Das kri  stallin -ausfallende     Bromacetimidoäthyläther-          bydrobromid    wird     abgenutseht    und nach    dem Auswaschen mit absolutem Äther zu  einer eisgekühlten     Lösung    von 15 Teilen       Äthylendiamin    in 2'50 Teilen     absolutem    Al  kohol unter gutem     Rühren    gegeben.

   Nach  etwa 1     Stunde    fügt man eine Lösung von  20 Teilen     Bromwaeeerstoffsäure    in     2150    Tei  len     absolutem    Alkohol     hinzu.    Das Gemisch  lässt man 2 Stunden bei     Zimmertemperatur     stehen und erhitzt es dann noch 1 Stunde  zum Sieden.

   Noch heiss wird dann vom aus  geschiedenen     Ammoniumbromid        abfiltriert.     Aus dem     Filtrat        kristallisiert    das     2-Brom-          m>ethyl-imidazolin-hydrobromi.d    in farblosen  Kristallen vom F.     201-202 .    Nach noch  maligem     Umkristallisieren    aus dem gleichen  Lösungsmittel     sehmilzt    es bei     20'6-20,9 .     



  Statt des     Bromacetimidoäthyläthers    kann  auch ein ,anderer Äther, wie z. B. der     Methyl-,          Propyl-,        Butyl-    oder     Phenyläther,    Verwen  dung finden.  



  An Stelle des     bromwasserstoffsauren     Salzes des     Bromacetimidoäthyläthers    kann  auch die freie Base selbst, oder ein anderes  Salz, wie z.     B,.    das Hydrochlorid oder      schwefelsaure Salz, als     Ausgangsmaterial    be  nützt werden.



  Process for the preparation of a reactive ester of an oayalkylamidine. It has been found that a new reactive ester of an oxyalkyl amidine can be obtained if a bromoacetimido ether is used with ethylenediamine. It is expedient to work in the presence of a solvent.



  The 2-bromomethyl-imidazoline of the formula obtained in this way
EMI0001.0011
    forms a colorless hydrobromide with a m. of 206 to 209. It is easily soluble in water. It should be used as an intermediate product. <I> Example: </I> 20 g of hydrobromic acid are introduced into a solution of 30 parts of bromoacetonitrile and 11.5 parts of absolute alcohol in 300 parts of absolute ether and the mixture is left at -1 'for 7 hours 0 stand.

   The bromoacetimidoethyl ether bydrobromide which precipitates out is removed and, after washing with absolute ether, added to an ice-cold solution of 15 parts of ethylenediamine in 250 parts of absolute alcohol with thorough stirring.

   After about 1 hour, a solution of 20 parts of hydrobromic acid in 2150 parts of absolute alcohol is added. The mixture is left to stand for 2 hours at room temperature and then heated to the boil for a further hour.

   The ammonium bromide which has separated out is then filtered off while still hot. The 2-bromine-m> ethyl-imidazoline-hydrobromide crystallizes from the filtrate in colorless crystals of F. 201-202. After repeated recrystallization from the same solvent, it melts at 20'6-20.9.



  Instead of the bromoacetimidoethyl ether, another ether, such as. B. the methyl, propyl, butyl or phenyl ethers, you will find use.



  Instead of the hydrobromic acid salt of bromoacetimidoethyl ether, the free base itself, or another salt, such as. B ,. the hydrochloride or sulfuric acid salt, be used as starting material.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines real :tion#- fähigen Esters eines Oxyalkylamidine, da durch gekennzeichnet, dass man einen Brom- aeetimidoäther mit Äthvlendiamin umsetzt. Das so gewonnene y2-Brommethy 1-imid- azolin der Formel EMI0002.0013 bildet ein farbloses Hydrobromid vom F. 246 bis 209 . In Wasser ist es leicht löslich. PATENT CLAIM: Process for the preparation of a real: tion # - capable ester of an oxyalkylamidine, characterized by the fact that a bromoetimidoether is reacted with ethylenediamine. The y2-bromomethy 1-imidazoline of the formula obtained in this way EMI0002.0013 forms a colorless hydrobromide from F. 246 to 209. It is easily soluble in water. Es soll als Zwischenprodukt Verwendung finden. UNTERANSPRüCHE: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man zur Um setzung B.ramacetimidoäthy läther verwendet. It should be used as an intermediate product. SUBClaims: 1. Method according to claim, characterized in that B.ramacetimidoethyether is used for the implementation. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man einen Brom- EMI0002.0024 acetimidoäther <SEP> verwendet, <SEP> der <SEP> aus <SEP> einem <SEP> Salz <tb> desselben <SEP> erhalten <SEP> wurde. <tb> 3. <SEP> Verfahren <SEP> nach <SEP> Patentanspruch <SEP> und <tb> Unteranspruch <SEP> ?, <SEP> dadurch <SEP> gekennzeichnet, <tb> dass <SEP> man <SEP> einen <SEP> Broinacetimidoätlier <SEP> verwen det, <SEP> der <SEP> aus <SEP> einem <SEP> Hydrohalogenid <SEP> desselben <tb> erhalten <SEP> wurde. <tb> d. Method according to claim, characterized in that one bromine EMI0002.0024 Acetimidoether <SEP> used, <SEP> the <SEP> from <SEP> a <SEP> salt <tb> of the same <SEP> received <SEP>. <tb> 3. <SEP> method <SEP> according to <SEP> patent claim <SEP> and <tb> Subclaim <SEP>?, <SEP> characterized by <SEP>, <tb> that <SEP> one <SEP> a <SEP> Broinacetimidoätlier <SEP> is used, <SEP> the <SEP> from <SEP> a <SEP> hydrohalide <SEP> of the same <tb> received <SEP>. <tb> d. <SEP> Verfahren <SEP> nach <SEP> Patentanspruch <SEP> und <tb> den <SEP> Unteransprüchen <SEP> ? <SEP> und <SEP> 3, <SEP> dadurch <SEP> ge kennzeichnet, <SEP> dass <SEP> man <SEP> einen <SEP> Bromacetimido äther <SEP> verwendet, <SEP> der <SEP> aus <SEP> einem <SEP> Hydrobromid <tb> desselben <SEP> erhalten <SEP> wurde. <tb> 5. <SEP> Verfahren <SEP> nach <SEP> Patentanspruch, <SEP> da durch <SEP> gelkennzeiehnet, <SEP> dass <SEP> man <SEP> in <SEP> Gegen wart <SEP> eines <SEP> Lösnii";sinittels <SEP> arbeitet. <tb> 6. <SEP> Verfahren <SEP> nach <SEP> Patentanspruch <SEP> und <tb> den <SEP> Unteransprüchen <SEP> 1 <SEP> bis <SEP> I. <SEP> dadurch <SEP> ge hennzeiehnet, <SEP> dass <SEP> man <SEP> Brom < acetimidoätlivl ä <SEP> Hier <SEP> verwendet, <SEP> der <SEP> aus <SEP> dein <SEP> Hvdrobromid <tb> desselben <SEP> erhalten <SEP> wurde. <SEP> method <SEP> according to <SEP> patent claim <SEP> and <tb> the <SEP> subclaims <SEP>? <SEP> and <SEP> 3, <SEP> marked by <SEP>, <SEP> that <SEP> one <SEP> a <SEP> bromoacetimido ether <SEP> is used, <SEP> the <SEP> from < SEP> a <SEP> hydrobromide <tb> of the same <SEP> received <SEP>. <tb> 5. <SEP> method <SEP> according to <SEP> patent claim, <SEP> because it is marked by <SEP>, <SEP> that <SEP> one <SEP> in <SEP> present <SEP> one < SEP> Lösnii "; works by means of <SEP>. <tb> 6. <SEP> method <SEP> according to <SEP> patent claim <SEP> and <tb> the <SEP> subclaims <SEP> 1 <SEP> to <SEP> I. <SEP> thereby <SEP> denotes, <SEP> that <SEP> one <SEP> bromine <acetimidoätlivl ä <SEP> here <SEP> used, <SEP> the <SEP> from <SEP> your <SEP> Hvdrobromid <tb> of the same <SEP> received <SEP>.
CH234926D 1938-05-11 1938-05-11 Process for the preparation of a reactive ester of an oxyalkylamidine. CH234926A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH229606T 1938-05-11
CH234926T 1938-05-11

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CH234926A true CH234926A (en) 1944-10-31

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3681379A (en) * 1969-04-26 1972-08-01 Basf Ag 2-carbamyl-2-imidazolines and method for their production

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3681379A (en) * 1969-04-26 1972-08-01 Basf Ag 2-carbamyl-2-imidazolines and method for their production

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